An α-(2-alkylcyclohexyloxy)-β-alkanol, especially a 1-(2-t-butylcyclohexyloxy)-2-alkanol, is a useful perfume material having a woody or amber-like fragrance and excellent persistence of aroma and capable of being inexpensively produced. For that reason, investigations regarding an efficient production method thereof are made.
For example, PTL 1 discloses (1) a method of converting a 2-alkylcyclohexanol by using a strong base into an alcoholate, which is then allowed to react with an epoxide; and (2) a method of allowing a 2-alkylphenol to react with an epoxide in the presence of a base catalyst, thereby forming an α-(2-alkylphenyloxy)-β-alkanol, which is then hydrogenated in the presence of a metal catalyst.
PTL2 discloses a method of producing hydrogenating an α-(2-alkylphenyloxy)-β-alkanol in the presence of a catalyst containing (a) a palladium catalyst and (b) one or more kinds of metal catalysts selected from ruthenium, rhodium, platinum, and nickel for the purpose of obtaining an α-(2-alkylcyclohexyloxy)-β-alkanol having an excellent fragrance and a high trans-isomer content in a high yield within a short period of time.
In addition, PTL3 discloses a method of producing an ether alcohol of subjecting a cyclic ketal to hydrogenolysis in the presence of a catalyst containing 50% by weight or more of palladium and less than 50% by weight of one or more kinds of members selected from ruthenium, rhodium, platinum, and nickel.